


you name the drama and i'll play the part

by Madfalldyn



Series: Commissions [73]
Category: Persona 5
Genre: Blow Jobs, Cunnilingus, F/M, Loss of Virginity, Nipple Play, Shotacon, Underage Sex, Vaginal Fingering, Vaginal Sex, commission
Language: English
Status: Completed
Published: 2020-12-03
Updated: 2020-12-03
Packaged: 2021-03-09 21:48:29
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,060
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27863330
Author URL: https://archiveofourown.org/users/Madfalldyn/pseuds/Madfalldyn
Summary: When she takes this job, Sadayo doesn't expect much from the client. Some son of a rich man, probably a spoiled brat. But when she comes face to face with the boy, she is surprised by how young he is. She's already taken the money, so there's no backing out now.
Relationships: Kawakami Sadayo/Original Character(s)
Series: Commissions [73]
Series URL: https://archiveofourown.org/series/1845484
Comments: 1
Kudos: 25





	you name the drama and i'll play the part

Sadayo doesn’t usually like to take on these sorts of jobs. They’re a bit more intense than the usual maid service work, that might end up leading into a massage, or letting some stressed out client lay on her lap for a while. That’s easy, not exhausting at all, but this? It’s a bit more involved, quite a bit, in fact. Obviously the pay is worth it, and ultimately why she can’t turn this particular job down.   
The family in question is a wealthy one, and willing to pay a premium for this particular service. They were even willing to pay up front, and quite a bit higher than the usual rate. She doesn’t question that, given the circumstances. They wanted to hire her to take their eldest son’s virginity, and to help teach him how to properly pleasure a woman. Something about the family’s reputation, so on and so on. Obviously, secrecy is key here, and much of the extra payment is a means to buy her silence.

It’s a bit weird, but with that much cash changing hands, Sadayo can’t really complain. It sounds like it’ll be a lot of work, but it’ll be worth it in the end. She gets ready as usual, once she’s finished with her day job. Dressing up in her maid outfit, putting all the usual effort into the changeover from Sadayo Kawakami to “Becky” the maid.   
The change isn’t only physical, either. She has to mentally prepare herself, to ready herself to become the playful and sweet maid she presents herself as, ever eager to care for whichever master has hired her for the night. She only hopes that tonight’s client isn’t some rich loser, unable to find a woman due to his terrible personality. Eldest sons of rich families can be quite a pain, as she’s learned all too well, and it’s hard to know exactly what she’s getting into.

Either way, she heads out, as ready as she’ll ever be. Of course, she couldn’t have known the situation she was getting into. Perhaps she should have questioned the pay more, or asked more about the situation. The large sum was enough to temper her caution, and as such, she will not be ready for what she is walking into. Not even close.

~X~

“Ah, there you are. Becky, isn’t it?” the man who opens the door for her asks. 

“That’s right, master,” Sadayo says, smiling, and bowing to the man. “I’m here for the maid service you requested.”

The man looks her over, checking her out pretty openly. They are sent photos of the maids in advance, of course, but most of her clients end up doing this sort of thing. It’s like a final check, making sure the product matches the photo, and while it’s a bit insulting at times, she can get it. It is a paid service, after all.

“Right, well, the young master’s room is just down the hall. We’ve informed him that you’re coming to help him today, and he is eager for what is to come,” the man says, and Sadayo assumes he must be some sort of servant. The voice doesn’t match the man who hired her, who said he was the father, and no one would refer to their own son as “young master.”

The wealth of this family begins to dawn on her, being greeted by some sort of butler, and with their opulence on full display within the house. Suddenly, all that money makes perfect sense. It’s no wonder they could afford to pay her so well, if this is how they live. She really, really hopes this young man isn’t some sort of spoiled brat, though it’s looking more and more like that might be the case.

She isn’t sure if she has the patience for that, but she’ll simply have to weather it. She’s already been paid, after all, and she’s not going to do a bad job now that money has already changed hands. Taking the money up front has plenty of benefits, but it also makes it so much harder to back out if things aren’t ideal. Whoever the young man waiting for her turns out to be, Sadayo is stuck with this.

“Thank you,” she says, bowing again. She begins heading for the room, walking calmly and professionally. She has to keep up appearances, even if she is beginning to worry about this job. The more she thinks about it, the weirder it becomes. Why so much money for this, if it’s just something basic? She should have asked more questions, should have gotten more detail, but it’s too late for that now.

She can beat herself up all she wants, but she’s stuck with this. Slowly, she reaches the door that the butler mentioned, and it is of course unlocked. With a light knock, she pushes it open, entering into the room. 

“Hello, master, your maid for the night is here,” she says, putting all of her heart into it. It doesn’t matter how worried she is, she has to put on a good show and play her part. She beams in, eyes closed, waiting for the voice that will inevitably greet her.

“Hello!” a voice calls out, but they sound… young. She opens her eyes, coming face to face with a boy in bed. A boy far too young for this sort of service. She is taken aback, blinking rapidly. What in the hell?

“Ah, there you are!” Sadayo says, trying to recover her composure. He’s so young, way too young, and yet, she knows she opened the right door. She couldn’t have messed up such simple instructions, there’s no way. “My name is Becky, and I’ll be serving you tonight.”

She tries to keep up her act, but her heart is racing. This kid is way, way too young. How did she get roped into this? Why didn’t she ask more questions? These rich families are always doing weird things, but she never thought she would be here to be some boy’s first time. The worst she expected was some bratty young man, given everything he ever wanted in life. This? She couldn’t have expected this.

She remembers what they wanted from her, that they specifically wanted her to teach the young master about how to pleasure a woman, how to be with a woman in a way that was satisfactory for both him and whoever he is with. She can do that, obviously, and it’s quite a bit better than simply giving yourself over to someone so they can vent their lusts upon you. But it’s a bit awkward now, given the kid’s age, and the way he looks at her. But, orders are orders, and she’s already been paid.

“You know what I’m here to help you with, don’t you?” she asks, and the boy nods. 

“Mhm, my dad said you’re going to come by and help me be a man,” he answers, and Sadayo has to admit, that’s kind of cute. In a weird, twisted sort of way. He’s way too young to be worried about that sort of thing, but he beams up at her, proud as can be. 

“Well, why don’t we go ahead and get started, then?” she asks, and again, the boy nods. “You’ve never done anything like this before, have you?”

It should be an obvious question, but who knows, given the circumstances. Sadayo wants to know if she’s starting from the ground up, or if there’s already some sort of foundation. She doubts it, and hopes there isn’t. Weird as it may be, she’d at least want to be the first one to be doing this with the boy. 

“Never, ever!” the boy answers, and Sadayo can at least feel a bit of relief at that. 

“Well, your father wanted me to teach you some things, okay?” Sadayo says, playing into her cutesy persona. She smiles down at the boy, trying her best to treat him like any other client. At least he doesn’t seem to be some spoiled brat, so far he’s actually pretty well behaved. That’s not much of a consolation, but she’ll take it.

“Alright!” the boy says, continuing to be agreeable. Slowly, Sadayo reaches up, tugging at the top of her dress. She pulls it down, exposing her breasts to him, and the look on his face is honestly rather flattering. He gawks at her, staring openly at her breasts, squirming a bit as he looks at her. 

“How does that make you feel?” Sadayo asks. It’s far from her first time working with kids, she may be a high school teacher, but it’s not like she’s never had to deal with some younger students. Of course, it doesn’t really translate perfectly to this particular job, but it is enough to get her in the right mindset. She is teaching him, so in a sense, he is a student of hers.

“Kind of funny,” the boy says, and Sadayo smiles.

“But good, right?” she asks, pressing the question.

“Yeah, it does,” the boy says, and Sadayo leans in closer.

“You can touch them, you know,” she says, pressing them together. With an arm at each side, she presents her breasts to him, and the boy slowly reaches up, cupping one of them. His hands are so small, a reminder of what she is doing in this moment, but somehow, there’s a thrill to that. It shocks her, to realize she thinks that, but some part of her… might actually be enjoying this?

He hesitantly touches her, and she can tell he’s already beginning to be overwhelmed. This is a lot for a boy his age, but she is willing to go as slow as she has to. She’s been paid plenty, far more than she could make in a night of ordinary work, perhaps even more than she could make in a week. If she has to take her time with him, that’s perfectly okay.

“They feel nice, right?” she asks, and the boy nods. “Here, watch this.”

She shifts, moving one hand to her own breast, squeezing and touching herself, until her nipple hardens beneath her touch. She takes it between two fingers, gently rolling them over it, moaning softly as she does. The boy watches intently, eager to be learning from her, a better student than most she has during the day.

“Do you think you could do that? It will feel really nice for your partner, and help to get her in the mood,” Sadayo says, and the boy nods. She pushes her breasts together once more, allowing the boy to try his hand at it. He is already more confident as he reaches up, doing just as she showed him, rolling her nipple between his fingers. He’s slower, not nearly as sure of himself as she was while showing him, but somehow, that makes his touch all the more appealing.   
His hands are soft, gentle, and Sadayo can’t help whimpering at his touch. He seems shocked at that, worried that he might have hurt her, but with a steady nod, urging him to continue, he doesn’t stop. He touches her, and Sadayo feels jolts of pleasure running through her body. It’s far from the first time she’s felt like this, but something about the look of absolute wonder on the boy’s face makes this feel better than she’s used to. 

“You can use your mouth, as well,” Sadayo says, and the boy does so. He leans in, pressing his lips to her other nipple, while continuing to play with the other. He looks so cute, latching onto her, gently suckling her as he rolls his tongue over her. He is learning quickly, far faster than she would have expected, and she can’t help herself. She reaches down, grabbing the back of his head, gently stroking him as he licks her and teases her. She moans, and that spurs him on, having already learned that that means she is enjoying herself.

She can’t believe how much she  _ is _ enjoying this. How much this is driving her mad, the feeling of this boy, doing his best to learn from her and pleasure her. It’s insane to think she would be getting off on this, enjoying this so much. It’s a side of herself Sadayo never should have come face to face with, but here she is. As the boy continues doing his best to pleasure her, she is surprisingly receptive to his touch. She already finds herself eager to continue with the lessons, to teach him more about her body. 

“Alright, that’s enough of that, we should move on to something else!” she says, and the boy doesn’t hesitate at all. He pulls back from her, so very obedient, and it’s no wonder Sadayo is enjoying this so much. He seems so eager to learn from her, so earnest, and it’s a far cry from the men she’s used to serving. This boy seems more interested in her and how she feels, even though she is only here to work. She rises from the bed, lifting her dress, slowly revealing her panties to the boy.

He gawks at her once again, squirming that same squirm, and it’s flattering to see how easily she can make him squirm for her. Sometimes, Sadayo worries she’s getting on in years. That this job won’t be feasible forever, but this boy doesn’t seem to notice or care about any of that. She’s the only woman he’s ever known, and he gawks at her, loving every bit of skin she shows him, How could she not love this?

“There’s plenty you can do down here, as well,” she says, continuing her lesson. “Do you want me to go through some of them?”

The boy nods, looking at her so intently as she speaks to him, and she finds herself blushing. Somehow, in all of this, she’s the one ending up embarrassed. He’s just so earnest, it’s impossible not to be a bit flustered by it all. 

“Alright, well, there’s options. Panties are nice, and this is a pretty nice pair. You can touch me over them, if you want,” Sadayo says, taking a step closer. He reaches out, gently touching the soft, silky fabric. It’s an investment, getting nicer pairs of panties like this, but in the end it always pays off. His touch is hesitant, just like before, but in no time he is tracing along the length of her cunt. She can’t help moaning at his touch, blushing down at the boy she is teaching. “Just like that, good job!”

At her praise, the boy blushes as well, seeming to enjoy it. He continues touching her, until she offers more guidance.

“If you’d like, you can push the panties aside, or pull them down. It’s personal preference, really, but some people just can’t seem to wait,” Sadayo guides him, and he opts for the former. He doesn’t want to wait to get to more, so he pushes them aside, exposing her cunt. He gasps at the sight of her, but is already moving to touch her, to feel the warmth of her pussy. 

“It’s so warm,” he comments, and it’s such an innocent comment considering all that’s going on. She feels her heart racing, pounding in her chest.

“That’s right, and you can push your finger inside of me, if you want,” Sadayo says. She’s surprised to find just how wet she is, soaked from this boy’s efforts already. It should be easy for him to finger her, especially given his size, and sure enough, he experimentally pushes inside of her. He sighs, softly, as the wet warmth of her cunt engulfs his finger. Sadayo cries out, loving the contact, and he is spurred on, working his finger in and out of her pussy. Before long, and without any prompting from her, he pushes a second finger inside, adding to the pleasure she feels.

“Ah, you’re doing great,” Sadayo comments, surprised to find just how true that is. This boy is doing better than most men, and she isn’t entirely sure if that’s some twisted preference hidden within her all this time, or simply natural skill on his part. Either way, she can’t help feeling pangs of guilt, but they are far outweighed by the arousal surging through her. She lets him finger her for a bit longer, before deciding to move on. “I have one final lesson for this bit.”

“What is it?” the boy asks, pulling back already. He is always so good about moving on, even if he seems to be enjoying himself. Sadayo sits on the bed beside him, spreading her legs. 

“You’ll have to get down off the bed for this bit,” she says, and he does so. “Now, come in, between my legs.”

He follows her orders, doing just as she asks, standing between her legs. He won’t even have to kneel to reach her, and some part of her knows she shouldn’t be so excited by that. She spreads her legs as much as she can, and begins to coax him in closer.

“You can use your mouth for that, as well, and it will feel absolutely amazing for your partner. If you can master that, there’s not much better,” Sadayo says, and the boy nods. He pushes in between her legs, not needing any further prompting. He seems to enjoy making her moan for him, seems to enjoy knowing that she is having fun. The praise she heaps on him helps, she’s sure, and as he buries his tongue inside of her, she can’t help but cry out.

“That’s a good boy,” she tells him, and he glances up at her, eyes bright and happy. As he works, slowly figuring out what she likes judging from her reactions, the boy is improving rapidly. He is such a fast learner, and Sadayo is losing herself in all of this. If he’s doing this good of a job with her, her lessons must really be working. Whatever woman this boy ends up with, Sadayo is sure she’s going to be happy with him. If how much she is enjoying herself is any indication, that is.   
His efforts have quickly shifted from clumsy to focus, and Sadayo is shocked to find herself at her very limit. She is crying out for him, whimpering praises, heaping them upon him, as she finally reaches her climax. All of his efforts have borne fruit, as her body begins to tremble at his touch, shaking from the force of her climax. She can hardly believe it, hardly believe one of the most powerful orgasms she’s felt has come from this boy, from teaching him how to pleasure a woman.

“Alright,” she says, a bit breathless from all of it. It’s time to move on, she knows, as good as this might feel. If she were to simply let the boy keep pleasuring her, it wouldn’t be in line with what she was paid to do. “I think it’s your turn, now. You’ve been such a good boy, and you deserve a reward!”

As Sadayo speaks, she pats the bed beside her. He hops up alongside her, wiping his face, and she shudders, knowing it is her arousal that covers him. Once he is on the bed beside her, she reaches over, unbuttoning his pajamas. She’s noticed his cock straining against the fabric for some time now, but he has been so patient, waiting for her to finish her lessons. She can’t wait to show him how much she appreciates that, and as she leans over pressing her lips to the tip of his cock, he cries out.

She parts her lips, taking his cock into her mouth with practised ease. She bobs her head up and down his length, rolling her tongue around him, showing him the other side of all of this. He has made her feel incredible, so it’s only fair he gets to feel every ounce of the pleasure she felt returned to him.

Sadayo is confident she can handle that, confident that as Becky, she can show him a time that rivals the time he showed her. In no time at all, he is twitching for her, already nearing his limit. He lacks endurance, of course, but that’s no surprise. Still, Sadayo doesn’t want him to blow his load this early on. She pulls back, and the boy whimpers, crying out at the lack of contact.

“It’s okay,” Sadayo says, “This is going to feel even better.”

She eyes his cock, feeling so eager for this, a hunger welling up inside of her. She needs him, needs this boy more than she’s ever needed anyone. She can scarcely believe how into this she’s gotten, how badly she aches for him, and she thinks she might just have to expand her services, including more along these lines if possible.

She eases him onto his back, straddling him. Reaching behind her, she lines the tip of his cock up with her entrance, still soaking wet from his efforts earlier. She can’t wait for this, she needs this, and slowly, she sinks down onto him. Onto the boy she’s taught so much, onto the boy that has made her feel far better than she ever could have expected. Her need to repay him is eclipsed by her desire for him, much to her surprise. Despite how young he is, she is desperate to ride him, to fuck him,

As his cock fills her, the boy cries out, squirming beneath her. He is unable to keep still, completely overwhelmed by the feeling of her tight pussy clinging to his young cock. He is so cute, looking up at her like she is whole world. She knows this doesn’t mean much to the family, that she is simply here doing a job, but part of her hopes this boy will remember her and her lessons forever. That the maid who helped make him a man one night, Becky, will live on in his mind for years to come. It’s a strange desire, but one she feels so strongly once it comes to her.

In a way, the thrill she feels now is better than anything she’s felt with this job in years. In truth, things were getting a bit stale, but this is just the spice she needed to feel re energized. She rides him frantically, desperately, bouncing on his cock.

She works her hips from side to side as she does, watching as the boy’s face shifts. She is overwhelming him, she knows, but she can’t stop. She can’t slow down. This feels too incredible, the way he looks at her, the whimpers and moans that escape him, it is all too intoxicating. Sadayo is shocked to find just how much she enjoys fucking this boy, and her idle thought from before returns to her.

If there’s truly a market for this, for families who want their young sons educated in the ways of fucking a woman, who want their sons to lose their virginities at this young age, perhaps there’s a market for this. Sadayo wants to try, to see if she can expand this service. Right now, with how incredible she feels, she hopes there is. In only a few more moments, the boy is there, crying out for her as he comes. Sadayo only barely manages to climb off of him in time, far too lost in the thrill to prepare for his climax. He comes on her, but she doesn’t stop grinding against him even as he does.

Desperately, she works herself to one final climax, grinding her cunt down against his leg as he comes, panting for her and gazing up at her. She has to expand this business, has to try and find more clients like this. This is the most fun she’s had with this job, and as Sadayo works to clean up, putting the boy down for bed and kissing him goodnight, she wonders where she should start.

He trip back home is filled with thoughts of how to progress this business, how to expand teaching and fucking boys. Perhaps, if she can pull it off, she’ll get to have a great time while getting rich. A woman can hope, right?

**Author's Note:**

> If you're interested in my writing, check out my Twitter for updates and information! https://twitter.com/MadfallWriting


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